


Clad in pink- A story of love, lust, and a large brightly colored strap on

by Raptarion



Category: Homestuck
Genre: Anal Fingering, Blow Jobs, F/M, Pegging, Plot What Plot/Porn Without Plot
Language: English
Status: Completed
Published: 2014-08-12
Updated: 2014-08-12
Packaged: 2018-02-12 20:46:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,402
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2124171
Author URL: https://archiveofourown.org/users/Raptarion/pseuds/Raptarion
Summary: <blockquote class="userstuff">
              <p>John Egbert and Roxy Lalonde have a sexual relationship. Every once in a while, they take a break from more vanilla activities to partake in something different. In this case, Roxy busting out her strap-on and taking John's ass to pound town.</p>
            </blockquote>





	Clad in pink- A story of love, lust, and a large brightly colored strap on

**Author's Note:**

> I originally commissioned two pictures of this scenario from the wonderful and talented Artist Crablouse. You can find them here.  
> http://crablouse.tumblr.com/post/94272979658

He could tell it was going to be a fun night. Which is true for most nights he got laid, but this night in particular. The normal routine of flirtation in the late afternoon to see if both he and Roxy were in the mood to knock boots had gotten a bit more frisky than usual. And when both of them were feeling frisky, that's when they decided to go above and beyond the relatively tame vanilla sexual practices. That was when they broke out handcuffs or blindfolds. Tried their hands at erotic roleplay or using hot wax. A few times they had even explored activities that they needed safe words for.

Of course, not all of the times they broke free of the vanilla routine was to try new things. Sometimes they returned to old favorites.

John looked up at Roxy, the sex toy she was sporting still lodged firmly in his mouth. She looked so sexy from this angle. Well to be accurate she looked sexy from pretty much every angle. But this particular angle seemed especially good. Maybe it was the way her cleavage was clung by her lingerie. Or maybe it was the infrequency with which he got to enjoy seeing her standing over him while he was on his knees. Apparently she liked the view too, judging by her expression.

John reaches up to grab onto one of her breasts, enjoying the softness and the feeling of the fabric. Roxy giggles a bit at this.  
"You always have such a one track mind. And that track always leads right to my tits apparently."

John grins around the strap on and squeezes, getting an appreciative moan from Roxy. He wasn't going to waste time justifying his love of her breasts. They were great. World quality even. Besides, it wasn't like those were her only assets he loved. Speaking of. He takes his other hand off of the sex toy he had been jerking off while he was blowing the rest. It was getting hard to get it any further down with his hand in the way anyway. He runs his hand up Roxy's thigh to grasp onto her ass. Yet another word quality body part. Easily worthy of a gold metal in any posteriors contest. Roxy reaches down to cover his hand. She squeezes down, encouraging him to do the same. He wasn't one to disappoint. He squeezes more roughly, and Roxy lets out another moan.

His hands now thoroughly occupied with groping his girlfriend, John focuses on taking in more of her girth. The hand curled up in his hair seemed to be a bit impatient for him to continue anyway, tugging him downward. Not all that hard mind. Roxy was fine with him taking the sex toy at his own pace (for now at least.) The tugs in his hair were light, and only mean to encourage him onward. In the beginning, that encouragement wasn't even needed. Roxy had only led his lips to the very tip. But he had taken much more than that rather quickly in his eagerness. Of course, he quickly had to slow down. Although he had taken this thing into his mouth on a fair number of occasions, he was by no means a master of blow jobs. Unlike Roxy, who seemed to have a god given mastery of giving head. John was still determined though.

Roxy tugged lightly to get him to go deeper. He got to the hard part, where the pseudo cock was pushing up against the back of his throat. He gags a bit as he tries to get it further. After a few seconds he has to pull back. Roxy eases up on the hair pulling to give him a chance to catch his breath. As soon as his breathing has evened out a bit she starts tugging again, encouraging inch after inch into his mouth. Once again it pushes up against the throat. Although it feels like he got further along this time, he soon enough has to pull back again.

He looks back up at Roxy. Although he's a bit frustrated at his limits, she doesn't seem to mind in the slightest, still getting a lot of pleasure from the push of the sex toy against her privates, and the view of her boyfriend going to town on her pseudo member.

John doesn't even wait for his breath to fully come back before going down again. He fully expects to get stuck again, but he manages to get the head of the toy past his stubborn throat! He coughs and gags in surprise, pulling back. He finally got it down. But not all the way yet. And he wasn't going to be satisfied with just getting the head of her member into his throat. He takes his time to collect his breath. Soon enough Roxy is lightly tugging on his hair, encouraging him to keep going. John is all to happy to oblige. He firmly grasps Roxy's ass with both hands as he goes down, using it as leverage to get more of the large strap on down his throat. Inch after inch disappears into his mouth, stretching out his throat all along the way. He kept forcing more of the pink cock down his throat, ignoring his gag reflex as his girlfriends artificial extension explored further and further into the tight wet recess of his esophagus.

Before he knew it, John had taken the entire thing. His mouth went forward to take more, only for his lips to hit the cloth of Roxy's panties. Somewhere along the way, Roxy had taken hold of the back of his head with both hands and had been pushing on the back of his head, a little harder than usual. The only thing between him and Roxy's pussy now, was a layer of fabric, and a large pink sex toy that was lodged firmly in his throat. John takes his view away from Roxy's midriff to look up at her face again. Roxy looked even happier than she did before, grinning from ear to ear at the sight of her boyfriend taking the entirety of her strap on for her. John likewise was enjoying his position, and the feeling of his throat being stretched out like this, combined with the view of Roxy clearly getting off, was pretty exhilarating. It easily topped the feeling of his dick straining against his boxers at the moment.

Unfortunately, all to soon he starts to gag, and the lack of air becomes uncomfortable. He pulls back off of the strap on, Roxy still holding onto his head, but not hindering his effort to pull up for air. As soon as John was off the cock Roxy stooped down to kiss him, not even giving him enough time to catch his breath properly. He spent the next few minutes trying to catch his breath and keep up with the tongue Roxy was shoving down his throat. Somewhere along the way he managed to get Roxy's bra off, as well as his boxers. The two of them were groping each other, grabbing each others ass, or breasts, or pulling their heads in closer. All the while both of their members were jamming into or rubbing against the other's pelvis.

But the best part of the evening was still to come, and so eventually Roxy broke off the kiss to grab some lube. John's saliva would only accomplish so much in making his imminent ass fucking easier after all. John rested his weight on his upper back and elbows, and propped his ass up for Roxy to get better access. Roxy let out a globule of lube onto her fingers as she eyed John's position with approval. She slathers some lube around his pucker before inserting a finger. John makes a conscious effort to not tighten up his ass at the foreign intruder. A task that was easier said than done, and had only gotten so much easier with time. Roxy wastes little time in inserting a second finger into his ass. She starts to slowly lather the inside of his ass with lubricant, taking time to massage his prostate every now and then, making it harder for him to not clamp down on her fingers. Every gracious stroke against that spot was amazing. If he had to compare, it probably felt better having his cock stoked. But the feeling of having is prostate massaged was entirely different. It was like trying to compare a chocolate cake to a rack of prime ribs.

Satisfied that the inside of his ass was adequately lubed for her insertion, Roxy withdraws her fingers. John almost whimpers at their retreat, but he didn't. He was about to get something to replace them soon enough after all. Roxy puts another globule in her hand and starts spreading it over her large pink member. She does this with agonizing slowness. But, eventually, she's done with the lube, and she crawls over and lines up the strap on to his anus. By this point, John's cock had leaked enough pre to create a strand connected to his stomach. Roxy rubs the tip of the pink cock against his entrance, and he struggles with the instinct to tense up.

Then, finally, she pushes forwards, and lodges the head into his ass.

His ass tightens up in spite of himself. Roxy looks at him, happily pushing forwards every so slowly. Angling herself to put pressure on his prostate. John tries to keep himself loose to accommodate her slow but relentless push into his bowels.  
"About a quarter of the way there." She says.  
A quarter? Couldn't be. There was so much already. She pushes some more, stopping only once when John grunts during a particularly tight moment. The halt in progress gives him enough composure to loosen up again, and Roxy continues.  
"Half way." She trills.  
She must be lying. This had to be more than half. It already felt like it was displacing most of his innards with its girth and length.  
"Three quarters of the way. Almost bottomed out." She said, sounding eager.  
They must have done this almost a dozen times before at least. But it always amazed him how MUCH of this damn cock there was. It felt like she had been pushing into him for hours.  
Then her pelvis made contact.  
"All in." She said happily.

Roxy stops there, giving him a moment to adjust. Damn did he feel full. He didn't think there was any more room in his ass. He was definitely at capacity.  
Almost as if on cure, Roxy starts rotating her hips. The mammoth strap on starts shifting around in the depths of his bowels, like it was trying to make room in the tight confines of his ass. He moans in response, and Roxy giggles again.

Apparently deciding that his ass was ready, she grabs hols of his thighs and lifts up a bit, helping him support his weight. Then, without further adieu, she starts thrusting. The thrusts start out long and deep and slow. Wanting to give time to get used to the feeling of getting his ass pounded. But over time she transitions to faster and rougher thrusting. John is perfectly fine with this, even if it is a bit painful. By the time Roxy really gets into the swing of things, he's biting his lip with a tear in his eye. But DAMN if this didn't feel amazing. Every thrust pushed up against him with such force. It threatened to knock his arms out from under him. His legs might have buckled already if Roxy wasn't helping keeping them propped up. And the length of that marvelous pink cock of hers became no less impressive. In fact, it seemed to hit him deeper and deeper as time went on.

Just as Roxy was at her peak, she suddenly bottomed out inside him, rubbing her crotch hard against her end of the sex toy as she moaned loudly. Her hands gripped his thighs tightly, and her body was going through miniature spasms as her face got lost in bliss. She was clearly going through a pretty strong orgasm. She started to come down from this and she grinned again, getting a wicked glint in her eye as she starts pounding away again, managing to go even harder than before. John's own orgasm wasn't very staved off by the halt in her thrusts. In fact, seeing Roxy get off like that brought him pretty damn close to the edge himself.

And as if the thorough ass fucking he was receiving wasn't enough, Roxy was now encouraging him to cum with dirty talk.  
"Oh you like that don't you John? Me hammering away at your ass like this. Your tight ass was practically made for this. You look like you're going to cum soon. Aren't you? We haven't even touched your dick and you're going to peak. Go on. Cum. Cum for me John."

The combination of the relentless thrusting and her words finally puts him over the edge. He loses himself in a haze as the feelings from his marvelously abused prostate radiate outwards. He think he called out Roxy's name, but he's too far gone at this point to notice.

A few seconds later he's down enough to get a good sense of his surroundings again. Roxy is once again buried deep inside him, but she isn't moving. She's looking down at John with a thoroughly satisfied expression. She's breathing deeply, and sweat accumulated from the exertion of fucking him literally senseless is dripping down all over her body. He lays still for a while longer, arms spread outwards, enjoying the afterglow of sex.

After a little while, Roxy slowly starts to pull out of his ass. It dislodges itself from his sphincter with a wet sound that Roxy snorts at. She removes the strap on and goes to put it away. She returns shortly and gives John another kiss. This one much shorter than their previous makeout session.

"I am going to be so sore in the morning." He comments.  
Roxy laughs at that.  
"Come on. Let's go to sleep. I'm exhausted."

John agrees and follows her to bed. They collapse onto the covers, to hot to bother with them, and curl up into each others arms, quickly dozing off.


End file.
